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DOI: 10.1055/s-2005-872239
Indium Trichloride Catalyzed Synthesis of 2-Aryl-3-aminobenzofuran Derivatives by a Three-Component Reaction of Phenols, Arylglyoxal Monohydrates and para-Toluenesulfonamide
Publikationsverlauf
Publikationsdatum:
22. Juli 2005 (online)
Abstract
A concise and efficient synthetic approach to 2-aryl-3-aminobenzofuran derivatives via an InCl3-catalyzed three-component reaction of arylglyoxal monohydrates, phenols and para-toluenesulfonamide has been developed. The benzofuran derivatives were obtained in good to excellent yields while the formation of α-diketones as by-products was effectively inhibited. The influences of reaction temperature, solvent and the order of the addition were also investigated.
Key words
benzofuran - phenol - indium trichloride - three-component reaction - arylglyoxal monohydrate
- 1a
Cagniant P.Cagniant D. Adv. Heterocycl. Chem. 1975, 18: 337 - 1b
Keay BA. Chem. Soc. Rev. 1999, 28: 209 - 2
Ohemeng KA.Apollina MA.Ngnuyen VN.Schwender CF.Singer M.Steber M.Ansell J.Argentieri D.Hagemann W. J. Med. Chem. 1994, 37: 3663 - 3
Kiyama R.Homma T.Hayashi K.Ogawa M.Hara M.Fujimoto M.Fujishita T. J. Med. Chem. 1995, 38: 2728 - 4
Nagahara T.Yokoyama Y.Inamura K.Katakura S.Komoriya S.Yamaguchi H.Hara T.Iwamoto M. J. Med. Chem. 1994, 37: 1200 - 5
Yang Z.Liu HB.Lee CM.Chang HM.Wong HNC. J. Org. Chem. 1992, 57: 7248 - 6
Su T.Naughton MAH.Smyth MS.Rose JW.Arfsten AE.McCowan JR.Jakubowski JA.Wyss VA.Ruterbories KJ.Sall DJ.Scarborough RM. J. Med. Chem. 1997, 40: 4308 - 7a
Engler TA.Gfesser GA.Draney BW. J. Org. Chem. 1995, 60: 3700 - 7b
Meshram HM.Sekhar KC.Ganesh YSS.Yadav JS. Synlett 2000, 1273 - 7c
Hu YH.Nawoschik KJ.Liao Y.Ma J.Fathi R.Yang Z. J. Org. Chem. 2004, 69: 2235 - 7d
Cacchi S.Fabrizi G.Goggiomani A. Heterocycles 2002, 56: 613 - 7e
Arcadi A.Cacchi S.Fabrizi G.Marinelli F.Moro L. Synlett 1999, 1432 - 7f
Willis MC.Talor D.Gillmore AT. Org. Lett. 2004, 6: 4755 - 7g
Park KK.Jeong J. Tetrahedron 2005, 61: 545 - 7h
Arcadi A.Cacchi S.Giuseppe SD.Fabrizi G.Marinelli F. Synlett 2002, 453 - 7i
Arcadi A.Cacchi S.Giuseppe SD.Fabrizi G.Marinelli F. Org. Lett. 2002, 4: 2409 - 7j
Macleod C.Mckiernan GJ.Guthrie EJ.Farrugia LJ.Hamprecht DW.Macritchie J.Hartley RC. J. Org. Chem. 2003, 68: 387 - 7k
Mckiernan GJ.Hartley RC. Org. Lett. 2003, 5: 4389 - 7l
Katritzky AR.Ji Y.Fang YF.Prakash I. J. Org. Chem. 2001, 66: 5613 - 7m
D’Sa BA.Kisanga P.Verkade JG. Synlett 2001, 670 - 7n
Lin SY.Chen CL.Lee YJ. J. Org. Chem. 2003, 68: 2968 - 8a
Hu YH.Zhang Y.Yang Z.Fathi R. J. Org. Chem. 2002, 67: 2365 - 8b
Li CC.Xie ZX.Zhang YD.Chen JH.Yang Z. J. Org. Chem. 2003, 68: 8500 - 8c
Liao Y.Reitman M.Zhang Y.Fathi R.Yang Z. Org. Lett. 2002, 4: 2607 - 8d
Wu MJ.Lee CY.Lin CF. Angew. Chem. Int. Ed. 2002, 41: 4077 - 8e
Bates CG.Saejueng P.Murphy JM.Venkataraman D. Org. Lett. 2002, 4: 4727 - 8f
Arcadi A.Cacchi S.Rosario MD.Fabrizi G.Marinelli F. J. Org. Chem. 1996, 61: 9280 - 8g
Hu YH.Yang Z. Org. Lett. 2001, 3: 1387 - 8h
Cacchi S.Fabrizi G.Mero L. Tetrahedron Lett. 1998, 39: 5101 - 8i
Bossharth E.Desbordes P.Monteiro N.Balme G. Org. Lett. 2003, 5: 2441 - 8j
Hughes CC.Trauner D. Angew. Chem. Int. Ed. 2002, 41: 1569 - 9a
Morice C.Garrido F.Mann A.Suffert J. Synlett 2002, 501 - 9b
Bach T.Bartels M. Tetrahedron Lett. 2002, 43: 9125 - 9c
Bach T.Bartels M. Synlett 2001, 1284 - 9d
Bach T.Bartels M. Synthesis 2003, 925 - 10a
Weber L. Drug Discovery Today 2002, 7: 143 - 10b
Dömling A.Ugi I. Angew. Chem., Int. Ed. Engl. 1993, 32: 563 - 10c
Dömling A.Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3169 - 11
Fayol A.Zhu JP. Angew. Chem. Int. Ed. 2002, 41: 3633 - For the leading references on the synthesis of similar aminobenzofuran derivatives, see:
- 12a
Ishikawa T.Miyahara T.Asakura M.Higuchi S.Miyauchi Y.Saito S. Org. Lett. 2005, 7: 1211 - 12b
Tsuji E.Ando K.Kunitomo JI.Yamashita M.Ohta S.Kohno S.Ohishi Y. Org. Biomol. Chem. 2003, 1: 3139 - 12c
Ando K.Tsuji E.Ando Y.Kuwata N.Kunitomo JI.Yamashita M.Ohta S.Kohno S.Ohishi Y. Org. Biomol. Chem. 2004, 2: 625 - 12d
Habermann J.Ley SV.Smits R. J. Chem. Soc., Perkin Trans. 1 1999, 2421 - 12e
Viti G.Giannotti D.Nannicini R.Ricci R.Pestellini V. J. Heterocycl. Chem. 1991, 28: 379 - 12f
Vaidya VP.Mahajan SB.Agasimundin YS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1981, 20: 391 - 14a
Ranu BC.Hajra A.Jana U. J. Org. Chem. 2000, 65: 6270 ; and references cited therein - 14b
Babu G.Perumal PT. Tetrahedron 1998, 54: 1627 - 15
Loh TP.Wei LL. Tetrahedron 1998, 54: 7615 ; and references cited therein
References
Unpublished results.
16
Typical Experimental Procedure.
Phenylglyoxal monohydrate (1a, 167 mg, 1.1 mmol), TsNH2 (171 mg, 1.0 mmol) and InCl3 (22 mg, 0.1 mmol) were mixed in 10 mL CH2Cl2 at r.t. and stirred for 30 min, then p-(t-Bu)PhOH (2a, 150 mg, 1.0 mmol) was added and the reaction system was warmed 40 °C. TLC showed
that the starting materials were consumed completely about 6 h and cooled the reaction
mixture to r.t. and 10 mL of H2O was added to quench the reaction. The aqueous layer was extracted with CH2Cl2 (3 × 20 mL) and organic solvent was combined and dried with anhyd Na2SO4. The solvent was evaporated and the residuum was purified by silica gel column chromatography
(EtOAc-n-hexane, 1:6 in volume) to give benzofuran product 3aa in 82% yield and its analytic data are as follows: mp 163-164 °C. IR (neat): ν =
3291, 2961, 1597, 1478, 1446, 1397, 1362, 1331, 1167, 1092, 883, 816, 768, 709, 690,
666 cm-1. 1H NMR (300 MHz, CDCl3): δ = 1.15 (s, 9 H), 2.27 (s, 3 H), 6.20 (s, 1 H), 6.81 (s, 1 H), 7.05-7.08 (d, 2
H, J = 8.1 Hz), 7.19-7.34 (m, 5 H), 7.57-7.59 (d, 2 H, J = 8.1 Hz), 7.86-7.89 (t, 2 H, J = 8.0 Hz). 13C NMR (75 MHz, CDCl3): δ = 21.5, 31.5, 34.6, 110.7, 112.5, 115.1, 123.1, 126.5, 127.5, 128.4, 128.6, 129.0,
129.0, 129.7, 136.9, 144.0, 146.2, 151.0, 152.1. HRMS (FAB): m/z calcd for C25H25NO3S [M]+: 419.1550; found: 419.1552. Anal. Calcd for C25H25NO3S: C, 71.57; H, 6.01; N, 3.34. Found: C, 71.38; H, 6.09; N, 3.13.